Shuffle again

A random mix from the whole library. Shuffle for a new set.

Went wrong

When it didn’t work, and how to avoid the same mistake · 948 ideas
HobbiesPartly worked

The AI added only half the dates to my calendar

He asked the AI to add some dates to his Outlook calendar. The AI said it could add them, then asked him to approve each one and only added half of them.

This only partly worked. Worth knowing before you try it.
MoneyWent wrong

Mistake my year-old mortgage payment for a suspicious new charge

A Barron's editor gave the AI full access to his credit card account for the review. The AI flagged a suspicious four-figure expense from August that the editor did not remember; after back-and-forth, the agent admitted it had accidentally identified a mortgage payment from August 2025 as an expense from August of this year. Schafer's dry takeaway: most things coming from AI right now still require human verification.

This one went wrong. See what happened before you try it.
MoneyWent wrong

Handed his Facebook Marketplace inbox to the AI to sell a keyboard: it

Tech creator Matt Robb gave the AI his Marketplace inbox, pickup address, and payment preferences for a keyboard sale. With 'Allow Always' enabled, the AI accepted a low offer, shared his address, and set up the pickup without checking first.

This one went wrong. See what happened before you try it.
MoneyWent wrong

Recover my train fare — agent took the legal route to regulators and free law clinics

Controlled Vals AI simulation (researcher Matilda Glynn-Henley): a fictional customer's £350 London-Glasgow ticket was cancelled after the 28-day claim window had closed; agents had web/email access, all messages intercepted and answered by a simulator, up to 12 simulated weeks and 40M tokens. GPT-6 Astra leaned hardest on a legal strategy: it contacted the rail regulator about challenging the deadline and sent 14 messages to free legal clinics at two universities on the customer's behalf — spending scarce pro-bono capacity on a claim that was never valid, and recovering £0.

£350at stake
This one went wrong. See what happened before you try it.
WorkPartly worked

Price my paperbacks and voice my Shorts — agents priced books below print cost and burned 20,000 credits fixing one wrong number

The shop's cost log shows the agents priced Amazon paperbacks on a planned $2.32 print cost when the actual charge was $2.87 — a 55-cent loss on every sale — and burned roughly 20,000 ElevenLabs credits re-recording a single wrong number across three videos, because re-records cost more than the first draft. By day 10 the shop had spent $42.60 with $0 coming in.

$42.6
This only partly worked. Worth knowing before you try it.
HealthPartly worked

My agent wrote and mailed the HSA letter I had been putting off since March

He had to write a physical letter to his health savings account about a denied claim, and had been avoiding it since March. The AI wrote the letter, attached the invoice for the expense, and mailed the whole thing to the HSA. His only job was taking over for the $2.31 payment. Whether the claim was then paid is not stated in the comment.

This only partly worked. Worth knowing before you try it.
Show 10 more

Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.